반응 #670022

반응 방정식

4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

aniline

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

수율 64.5%

N-Phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

수율 64.5%

용매

dioxane

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   온도The residue was cooled in an ice water bath
3. 3
   workup.ADDITIONaqueous 3.6N hydrochloric acid was added
4. 4
   기타the precipitate collected
5. 5
   세척rinsed with aqueous 3.6N hydrochloric acid
6. 6
   건조water and dried
7. 7
   기타Recrystallization from ethyl alcohol

실험 절차

A mixture of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol), aniline (0.46 mL, 5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (959 mg, 5 mmol) in 50% aqueous dioxane (10 mL) was allowed to stir at ambient temperature for 17.5 hours, then concentrated in vacuo. The residue was cooled in an ice water bath, aqueous 3.6N hydrochloric acid was added, and the precipitate collected, rinsed with aqueous 3.6N hydrochloric acid then water and dried. Recrystallization from ethyl alcohol afforded N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (Compound 35) (164 mg). mp 225-226° C.

출처